Process of making explosive compounds and product thereof



with timid CHARLES TE. STINE, OF 'WILTJII'NGTCN, DELAWARE, ASSIZGNOR 'lGE. 1'. m3 FONT DE NEMO'P'RS AND COMPANY, 033 WIL'MINGTON, DELANAEBIE, ACORPORATION OF DELA'WABE.

PROCESS OE MAKING EQPLOSIVE COIIZ'PDUNDS AND EROTD'UCT N0 Drawing.Application filed May 31,

To all whom it may concern Be it known that I, Cnaanus Smnn, of liilmington, in the county of New astle, and in the State of Delaware,have invented a certain new and useful improvement in Processes oflinking Explosive Compounds and Product Thereof, and do hereby declarethat the following a full, clear, and exact description thereof.

My invention relates particularly to a process for producing explosivesof an acvantageeus character, and the product thereof. The object of myinvention is to provide a process for producing explosives andparticularly explosive compounds containing a nitro group and nitrategroups, or a plurality of nitro groups and nitrate groups, and theproduct produced thereby. A further object of my invention is to providecompounds of this character tin which. a nitro group is located in thering of a molecule of an aromatic compound and a plurality of nitrategroups are located in one side chain of the compound.

While my invention is capable of embodiment in many different forms, forthe purpose of illustration 1 have described only certain forms thereo For example, I may proceed as follows:

The compound produced in accordance with my process may be, for example,any one of the followin u i- W Q A M Q.) 2 one .crn. cnqnoncn no non,06H .on,1vo on uo, .c neonates, c n, cn cn.no,.cn .no ,),(NO,),

c non.wnnmcrnno,

(cn.no,.ou,.no, ,no, c non cnno cn n p. n0

,and secondary carbon atoms of the side chain. The chlorinated compoundis then Specification of Letters Yatent.

1917. Serial No. 171,980.

nitrated preferably in the ordinary Way by applying a mixture of nitricand sulfuric acids according to the procedure usually followed innitration. preferably until the dinitro compound obtained. The nitratedmaterial is heated with pure water, preferably under a pressure or":about 20 pounds per square inch, until the. chlorin atoms in the sidechain have been replaced by hydroxyl groups.

The aqueous solution is then evaporated to drive off he water andhydrochloric acid, and the dinitrophenyl compound is nitrated furtheraccording to the well known method by the application. of a mixture ofsulfuric .m :l nitric acids resulting in substituting a nitrate group1201' each hydroxyl group in a side chain. The material thus obtained,which can be separated from the spent acid, or which may be obtained bydrowning the spent acids with subsequent separation, is, after drying,suitable for use as an explosive or an ingredient in explosives. Theexplosive thus obtained is exceedingly powerful and quite stable.

Y I buch compounus by other processes, tion of an aromat.

iay also be prepared I or example, a nitraf hydrocarbon containing atleast one side chain to the 11101101 di-, or tri-nitro compound,chlorination of the dinitro compounds to cause chlorin to becomeattached to carbon atoms of the side chain. hydrolysis of thechlor-nitro compound to produce a nitro hydroxyl compound and nitrationof the nitro-hydroxyl compound to produce a nitro nitrate.

While I have described my invention above in detail, I wislr it to beunderstood that many changes may without departing from the spirit of myinvention. For example, i. do not wish to limit myself to preparation,and I wish it to be understood that the compounds produced in accordancewith my invention may be used as such or in ixtures of various kinds, asdesired.

l claim: i

1. A process of producing an explosive compound which comprisesnitratingand halogcuatiug: an aromatic compound which contains a side chainci'n'uprising an alkyl be made therein any particular method of with aplural carbon nucleus so as to i11-' troduce a nitro group into themolecule and a plurality of halogen atoms into the side I producing anexplosive compound which comprises nitrating and halo 'enating abenzenoid hydrocarbon whic contains a side chain comprising an alkylwith a plural carbon nucleus so as to introduce a nitro group into themolecule and a plurality of halogen atoms in the side chain, hydrolyzingto substitute hy droxyl groups for the halogens, and nitrating tosubstitute nitrate groups for the by droxyl groups.

'3. A process of producing an explosive compound which comprisesnitrating and halogenating a hydrocarbon of the aromatic series whichcontains a side chain comprisingan alkyl with a plural carbon nucleus soa'sto introduce a nitro group into the molecule and a plurality ofhalogen atoms into the side chain, hydrol Zing to .substitute hydroxylgroups for t e halo- ,gens, and nitrating groups for the liydroxylgroups.

4. process of producing an explosive compound which comprises nitratingand halogenating a hydrocarbon of the aromatic series which contains aside chain comprising an alkyl with a plural carbon nucleus so as tointroduce a into the ring and a plurality of halogen atoms into the sidechain, hydrolyzing to substitute hydroxyl groups for the halogens, andnit-rating to Substitute nitrate groups for the hydroxyl groups.

5. A process of producing an explosive compound which comprisesnitrating and :halogenating ethyl benzol so as to introduce a nitrogroup into the ring and a plurality of halogen atoms into ,the sidechain, hydrolyzing to substitute hydroxyl groups for the halogens, andnitrating to substitute nitrate groups for the hydroxyl groups.

6. A process of producing an explosive compound which comprisesnitrating and halogenating ethyl benzol so as to introduce a pluralityof nitro groups into the ring and a plurality of halogen atoms into theside chain, hydrolyzing to substitute hydroxyl groups for the halogens,and nitrating to substitute nitrate groups for the hydroxyl groups.

.A process [of producing an explosive compound which comprises nitratingand alogenating an aromatic, compound which contains a side chaincomprising an alkyl 'with a plural carbon nucleus so as to introduce anitro group into the molecule and a plurality of halogen atoms into theside chain, hydrolyzing to substitute hydroxyl ,groups for the halogens,and nitratin to substitute nitrate groups for the hydroxyl to substitutenitrate plurality of nitro groups being carried out groups, thehalogenation being carried out before the initial nitration.

8. A process of producing an explosive compound which comprisesnitrating and halogenating a hydrocarbon of the aromatic series whichcontains a side chain comprising an alkyl with a plural carbon nucleusso as to introduce a nitro group into the molecule and a plurality of;halogen atoms into the side chain, hydrolyzing to substitute hydroxylgroups for the halogens, and nitrating to substitute nitrate groups forthe hydroxyl groups, the halogenation being carried out before theinitial nitration.

9. A process of producing an explosive compound which comp isesnitrating and halogenating an aroma 10 compound which contains a sidechain comprising an alkyl with a plural carbon nucleus so\ as tointroduce a plurality of nitro groups into the molecule and a pluralityof halogen atoms into the side chain, hydrolyzing to substitute hydroxylgroups for the halogens, and nitrating to substitute nitrate groups forthe hydroxyl groups,. the halogenation being carried out before theinitial nitration.

10. A process ofproducing an explosive compound which comprisesnitrating and halogenating a hydrocarbon of the aromatic series whichcontains a side chain comprising an alkyl with a plural carbon nucleusso as to introduce a plurality of nitro groups into the ring and aplurality of halogen atoms into the side chain, hydrolyzing tosubstitute hydroxyl groups for the halogens, and nitrating to substitutenitrate groups for the hydroxyl groups, the halogenation before theinitial nitration.

11. A process of producing an explosive compound which comprisesnitrating and halogcnating ethyl benzol so as to introduce a nitro groupinto the ring and a plurality of halogen atoms into the side chain,hydrolyzing to substitute hydroxyl groups for the halogens, andnitrating to substitute nitrate groups for the hydroxyl groups, the.halogenation being carried out before the initial nitration.

12. A, process of producing an explosive compound which comprises,nitrating and halogenating ethyl benzol so as to introduce a pluralityof nitro groups into the ring and a plurality of halogen atoms into theside chain, hydrolyzing to substitute hydroxyl groups for the halogens,and nitrating to substitute nitrate groups for the hydroxy.". groups,the halogenation being carried out before the initial nitration.

13.1A'n explosive comprising an organic compound of the aromatic serieshaving a side chain, said compound containing 9. nitro group and havinga plurality of nitrate groups in the side chain.

14.,An explosive comprising an organic compound of the aromatic serieshaving a nitro groups and having a plurality of niside chain andcontaining a plurality of nitro groups and having a plurality of nitrategroups in the side chain.

15. A. composition containing an organic compound of the aromatic serieshaving a side chain, said compound containing a nitro group and having aplurality of nitrate groups in the side chain.

\ 16. A composition containing an organic compound of the aromaticseries having a side chain and containing a plurality of I have hereuntoset my trate groups in the side chain.

17. An organic compound of the aromatic 15 series having the formula c nrcnno on uo No In testimony that I claim the foregoing hand.

CHARLES M. STINE. Witnesses E. K. BoL'roN, P. E. STRIOKLAND.

